Aaron was a master at making conversation with anyone, from Prince Charles to the busboy at a restaurant. Unfortunately, chatting with strangers doesn’t come easily for many of us. As I wrote in Candy at Last, Aaron and I spent our third or fourth date working on improving my social skills.  Here are a few tips I’ve picked up on how to gracefully make small talk so that the conversation isn’t awkward and is even enjoyable:

Start with a cheery observation.  One way to open small talk is by commenting on the situation you are both in (“What a great party” or “Such a long line—the coffee here must be delicious”).  Try to keep it positive or humorous. This will help to disarm and put the person you’re speaking to at ease.

Ask questions.  It’s a cliché that asking lots of questions is the key to being a great conversationalist. While there’s some truth to that, your questions shouldn’t be too pointed. After all, asking about things like work or relationship status may be touchy topics (maybe the person just lost a job or is going through a divorce).  Better to keep your questions light at first.  “What are you up to this weekend?” is always a good one, because the person’s response will tell you something about him or her and let you know where the conversation should go. For example, if she is traveling you can talk about favorite destinations, but if he reveals that he’ll be visiting a sick parent or tending to some similar personal matter then you know you can take the conversation deeper.

Avoid yes or no questions.  Questions like “Are you watching the World Cup this weekend?” can lead to a conversational stand still if the answer is “no.”

Don’t stress. If the other person is terse or seems unfriendly, try not to take it personally–he or she is probably just shy and not a skilled small talker!  When it’s time to wrap it up, look the person in the eye and say “It’s been so nice talking with you” in a sincere tone and then move on to your next conversation.

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